Palladium‐Catalyzed Annulation of Arylbenzamides with Diaryliodonium Salts

Abstract

By using diaryliodonium salts, a cylization has been accomplished in the synthesis of Naryl phenanthridinone derivatives via a cascade of ortho-arylation and Csp 2 -N bond formation in the presence of palladium catalyst. The reaction exhibits a broad compatibility of readily available Narylnaphthamides.

Reactions of 3-Hydroxy-2-phenyl-1H-benzo[e]isoindol-1-one: A Route to 3-Hydroxy-/3-anilinobenzo[e]indan-1-ones and Benzo[f]phthalazin-1(2H)-ones

“…N -Phenylnaphthalene-1-carboxamide [ 42 , 43 , 44 ], 3-hydroxy-2-phenyl-2,3-dihydro-1 H -isoindol-1-one 2 [ 45 ], and 2-[2-(dimethylamino)ethyl]-2 H -phthalazin-1-one 19 [ 39 ] were obtained as described previously; their characterization data were in agreement with the reported analysis. The characterization data of 2-(2-methylpropanoyl) benzaldehyde 8 [ 26 ] and 3-hydroxy-2,3-dihydro-1 H -inden-1-one 5c [ 46 ] were in agreement with the already reported analysis.…”

Tandem Palladium/Copper-Catalyzed Decarboxylative Approach to Benzoimidazo- and Imidazophenanthridine Skeletons

“… 13 The key regioselectivity-determining step in the major pathway, that is, reductive elimination in intermediate D , represents a highly unusual example of the preferential formation of a C–N rather than C–C bond in Pd species featuring two phenyl ligands and one amide ligand. 14 Here, the observed selectivity can be potentially attributed to the oxidation state of the palladium center, Pd II , as the opposite selectivity was observed for reductive elimination from Pd IV species.…”

Diaryliodonium Salts Enabled Arylation, Arylocyclization, and Aryl‐Migration

“…By using diaryliodonium salts, a cyclization has been accomplished in the synthesis of N-aryl phenanthridinone derivatives via benzocyclization in the presence of palladium catalyst. [27] The reaction exhibits a broad compatibility of readily available N-aryl-naphthamides. 40 examples of N-aryl phenanthridinone derivatives were prepared via ortho-arylation and Csp 2 -N bond formation.…”

“…Besides carboxylic acid as directing group, amide group of Ar‐NHCO was also investigated for the directing effect. By using diaryliodonium salts, a cyclization has been accomplished in the synthesis of N ‐aryl phenanthridinone derivatives via benzocyclization in the presence of palladium catalyst [27] . The reaction exhibits a broad compatibility of readily available N‐aryl‐naphthamides.…”